Bufadienolides. Part XXIII. 14,15β-Epoxy-3β,11α-dihydroxy- 5β-bufa-20,22-dienolide (11α-hydroxyresibufogenin)

George Pettit, Yoshiaki Kamano

Research output: Contribution to journalArticle

5 Citations (Scopus)

Abstract

Synthetic procedures have been developed for conversion of gamabufotalin (3β,11α,4-trihydroxy-5β-bufa-20,22-dienolide) (1a) into 11α-hydroxyresibufogenin (5a). Selective dehydration of gamabufotalin with hydrochloric acid in metnanol gave the 14-ene (2a). Addition of, for example, hyprobromous acid to this olefin (2a) afforded the bromohydrin (4b) which upon treatment with pyridine easily afforded 11α-hydroxyresibufogenin. As part of this study 11α-hydroxybufalone (11α,14-dihydroxy-3-oxo-5β- bufa-20,22-dienolide) (3a) was also prepared.

Original languageEnglish (US)
Pages (from-to)725-727
Number of pages3
JournalJournal of the Chemical Society, Perkin Transactions 1
StatePublished - 1973

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Bufanolides
Hydrochloric Acid
Alkenes
Dehydration
Acids
pyridine
bromohydrins

ASJC Scopus subject areas

  • Chemistry(all)
  • Medicine(all)

Cite this

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abstract = "Synthetic procedures have been developed for conversion of gamabufotalin (3β,11α,4-trihydroxy-5β-bufa-20,22-dienolide) (1a) into 11α-hydroxyresibufogenin (5a). Selective dehydration of gamabufotalin with hydrochloric acid in metnanol gave the 14-ene (2a). Addition of, for example, hyprobromous acid to this olefin (2a) afforded the bromohydrin (4b) which upon treatment with pyridine easily afforded 11α-hydroxyresibufogenin. As part of this study 11α-hydroxybufalone (11α,14-dihydroxy-3-oxo-5β- bufa-20,22-dienolide) (3a) was also prepared.",
author = "George Pettit and Yoshiaki Kamano",
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journal = "Journal of the Chemical Society, Perkin Transactions 1",
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T1 - Bufadienolides. Part XXIII. 14,15β-Epoxy-3β,11α-dihydroxy- 5β-bufa-20,22-dienolide (11α-hydroxyresibufogenin)

AU - Pettit, George

AU - Kamano, Yoshiaki

PY - 1973

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